Search Listings:

Where the Boys Are!

"You can teach them tricks," says a 36-year-old public-relations executive who recently had a three-month-long affair with a friend's younger brother.

"It's like walking into battle with a veteran general," says Ben of his first night with Suzanne. "There's also some magic to that feeling of 'What will I find?' There's always that when it's a new relationship, but the age thing made me even more curious. You kind of unwrap the package with your eyes half open."

He wasn't disappointed. "Older women spend more time working on those things," Ben says, choosing his words carefully to avoid getting too clinical. "Let's just say she would wax."

Jane Pratt, 39, the editor-in-chief of Jane magazine and a close observer of trends in women's lives, is expecting her first baby in December. She is engaged to the father, Andrew Shaifer, 36. Younger men run in Pratt's family. "My mom's been married three times," she says, "and always to younger guys. Her current husband is seven years younger. My grandma was married to a younger man for 70 years. It's funny: As soon as I told my family and friends I was really serious about Andrew, they asked, 'How old is he?' They were afraid I was going to go for 25, so when I said 36, there was a huge sigh of relief."

For Pratt, who has always dated younger, the appeal has everything to do with work and career. "When I started Sassy magazine, I was 23. I had a boyfriend at the time -- Bryan -- and I broke up with him. I said, 'I'm just not going to have time.' " She didn't have another serious boyfriend for years.

"I really do think it's a New York phenomenon," she says. "No one bats an eye if a woman is dating a guy ten years younger. If anything, they kind of give you the thumbs-up. I try to move around a lot so people can't see my wrinkles."

Younger men are often less threatened by a powerful career woman; in fact, all that female power can be something of a turn-on. "I like strong women who are driven," says Shaifer, a successful actor-screenwriter in his own right, who proposed to Pratt at a dinner in L.A. attended by friends Courteney Cox and David Arquette, another OWYM couple. "When we check into L'Hermitage when she's out in L.A. on business, they call me Mr. Pratt. But I'm not intimidated by it. She's the total package. My main attraction to her is because she's smarter than me."

Many career women aren't looking to fit into a man's schedule; they are looking for a man to fit into theirs. (An extreme example is Suzy Wetlaufer, the Harvard Business Review editor who installed a 22-year-old male editorial assistant in her basement, presumably for easier availability.) "Women can pick and choose," says Pratt. "They are supporting themselves, so they can go for younger, they can go for older, they can go for whatever they want."

Oscar Blandi, the hairstylist who tends the locks of Natasha Richardson and Jennifer Connelly, has noticed that the women in his chair -- even the 50-year-olds -- are looking younger than ever, and younger men are an ever-more-frequent topic. "I grew up with the idea that men age better than women," says Candace Bushnell. "That's just not true anymore. The truth is, all the women in New York look 35!" Gyms are the churches of this youth movement, and the high priest is David Kirsch, who trains models like James King and Heidi Klum at Madison Square Club on Fifth Avenue, where the younger clients give his older clients the incentive to squeeze into their own Seven jeans. "They're very focused and disciplined," says Kirsch. "They point to the younger ones and say, 'Oh, my God, she looks great! I love her butt. How do we do that?' "

From Sela Ward to Meg Ryan to Madonna, fortysomething is the new thirtysomething, and if you don't look the part, you have only your personal trainer to blame. Madonna, as always, is a reliable Zeitgeist meter, and at 43, she is embracing the role of sexy older woman. First, there was her recent marriage to 33-year-old film director Guy Ritchie, and now Ritchie has directed her in this fall's remake of the seventies Italian classic Swept Away, in which she plays a wealthy hottie shipwrecked on a deserted island with a 31-year-old Italian working-class hunk.

"The fact that they're even making these movies is a breakthrough," says Bushnell. "A lot of Hollywood is run by men, and they want to see their fantasies. These are female fantasies -- great sex with a younger guy. It really shows that things are changing."

In real life, OWYM relationships are subject to their own unique set of stresses, and Hollywood happy endings aren't guaranteed. There's the clash over income imbalances, as when an investment banker, 41, and her younger boyfriend started talking rings. For them, the dilemma wasn't princess-cut versus round. "You can't afford the ring I want," she told him, "and I don't want the ring you can buy."

There are the mismatched cultural references that pop up at awkward moments. "My girlfriend went back to this guy's house and was looking at his CDs," says Pratt. "The first CD he bought was Pearl Jam. She was like, 'That's just too much. That's too big of a gap.' " For the younger partner, there's the fact that everything he is just now feeling, she experienced long before. "I lived in the East Village," says Ben, "but Suzanne lived in the East Village for ten years -- ten years ago. Everything I did, she'd already done."